Trifluoroacetic acid → 3-(1-adamantyl)4-methoxy-N-(trifluoroacetyl)aniline

HRID 235310

반응식

HRID 235310 반응식
C([N:3](CC)CC)C.ClC(OCC)=O.[C:14]12([C:24]3[CH:25]=[C:26]([CH:30]=[CH:31][C:32]=3[O:33][CH3:34])C(O)=O)[CH2:23][CH:18]3[CH2:19][CH:20]([CH2:22][CH:16]([CH2:17]3)[CH2:15]1)[CH2:21]2.[N-]=[N+]=[N-].[Na+].[F:39][C:40]([F:45])([F:44])[C:41](O)=[O:42].C(=O)(O)[O-].[Na+]>O1CCCC1.O>[C:14]12([C:24]3[CH:25]=[C:26]([CH:30]=[CH:31][C:32]=3[O:33][CH3:34])[NH:3][C:41](=[O:42])[C:40]([F:45])([F:44])[F:39])[CH2:21][CH:20]3[CH2:22][CH:16]([CH2:17][CH:18]([CH2:19]3)[CH2:23]1)[CH2:15]2

참가 물질

9

반응물 6

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 33557Sodium AzideHCID 516892Sodium BicarbonateHCID 52965033-(1-Adamantyl)-4-methoxybenzoic acid

생성물 1

HCID 190682803-(1-adamantyl)4-methoxy-N-(trifluoroacetyl)aniline수율 57%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매3회

반응 조건

온도
0 °C

실험 절차

11.70 ml (84 mmol) of triethylamine in 10 ml of tetrahydrofuran and 8.70 ml (91 mmol) of ethyl chloroformate in 10 ml of tetrahydrofuran are successively added dropwise to a solution of 20.6 g (70 mmol) of 3-(1-adamantyl)-4-methoxybenzoic acid in 200 ml of tetrahydrofuran at 0° C. The reaction medium is stirred for 40 minutes at 0° C., 6.83 g (105 retool) of sodium azide, dissolved in 30 ml of water, are then added to this medium and the mixture is left stirring at 0° C. for 2 hours. The reaction medium is poured into ice-cold water, the mixture is extracted with dichloromethane and the organic phase is washed with water, dried over magnesium sulphate and evaporated. The residue is dissolved in 400 ml of dichloromethane, 7.3 ml (0.094 mol) of trifluoroacetic acid are added and the mixture is heated to reflux for 30 hours. The reaction medium is poured into saturated sodium bicarbonate solution and the organic phase is dried over magnesium sulphate and evaporated. The residue is chromatographed on silica with a dichloromethane/hexane (30:70) mixture to yield 14.1 g (57%) of 3-(1-adamantyl)-4-methoxy-N-(trifluoroacetyl)aniline, melting point 166°-167° C.

후처리

  1. additionare then added to this medium
  2. waitthe mixture is left
  3. stirringstirring at 0° C. for 2 hours
  4. additionThe reaction medium is poured into ice-cold water
  5. extractionthe mixture is extracted with dichloromethane
  6. washthe organic phase is washed with water
  7. dry with materialdried over magnesium sulphate
  8. customevaporated
  9. dissolutionThe residue is dissolved in 400 ml of dichloromethane
  10. temperaturethe mixture is heated
  11. temperatureto reflux for 30 hours
  12. dry with materialthe organic phase is dried over magnesium sulphate
  13. customevaporated
  14. customThe residue is chromatographed on silica with a dichloromethane/hexane (30:70) mixture

출처 및 근거

ORD 기록
ord-c8dbc984b44b4365aa8244b736d5a392
출처 데이터셋
uspto-grants-1997_01
특허 번호
US05597839

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